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It's certainly possible considering quite a bit of Houston is sprawl from what I gather, but I unfortunately don't know enough about Houston's city limits or density to really make much of an educated guess. Chicago's city limits are, for the most part, all built up and fairly dense to very dense at this point. I could be wrong, but I don't believe the same can be said of Houston.

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Haha no, Houston 600 mi sq, Chicago 234 mi sq. To put it in perspective, Chicago has only 40% the land area Houston does, with more than 600k people. Houston is a great town. Been there a few times, love it. It's entirely possible that Houston could eclipse Chicago based on its sheer land mass. But that still wouldn't accurately reflect the size of the two cities. Chicago is a metro area of more than 9milliion people. Last I saw Houston was pushing 6mil. Technically any city could grow it's population by expanding it's borders, but it's still not an accurate comparison of two regions. I wish there were more analysis to city populations than just municipal boundaries. So many of the sunbelt states like TX, AZ,and NV have very lax laws when it comes to cities annexing outlying areas. Which is why Cities in those states seem so populous. Where as states like Ohio, IL, and Michigan, have archaic township laws, where there is literally not a square inch of land in the state that is not incorporated. Making it difficult if not impossible, to expand civic boundaries. Which is why cities like Grand Rapids, Cleveland, and St Louis to name a few, have larger metropolitan areas than their national city rankings might reflect.